


Out of My League

by CuriousBones



Category: Supernatural (TV)
Genre: F/M, Fluff, Happy Ending, Insecure Dean, Love Confessions, insecure reader
Language: English
Status: Completed
Published: 2016-06-25
Updated: 2016-06-25
Packaged: 2018-07-18 03:20:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,063
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7297411
Author URL: https://archiveofourown.org/users/CuriousBones/pseuds/CuriousBones
Summary: <blockquote class="userstuff">
              <p>Reader has feelings for Dean but knows he could never feel the same. However, after a heart-to-heart with the great big moose himself, Reader decides to finally admit her feelings to Dean. And, of course, it's in a bar. Where else would you find the liquid courage to do something so bold?</p>
            </blockquote>





	Out of My League

You tap your fingers on your leg to the beat of the song blasting through the speakers. Looking out the window into the endless plains, you enjoy the beauty of your surroundings. Sure, the country outside the car is beautiful, but your mind is on the green-eyed blond driving the car in the seat in front of you. 

You had known Sam and Dean Winchester for years. Really, since you were a kid. Your parents were hunters, and good friends of Bobby and John. Usually, they went on hunts with John if they were close by, and they would leave you with Bobby and the boys. 

You had always been closer to Sam platonically. He was your best friend in the world, and you felt safer with no one else. Dean was a close second, but your relationship was… different with him. Sure, you laughed together, made jokes and spent most of your time together, but you had always felt different about him. Maybe it was how his pale freckles danced across his nose playfully when he laughed, or how his eyes twinkled when he smiled. Maybe it was how he could switch from best friend to flirt in half a second, or how he could always make you smile, even when you felt like digging a hole in the ground and dying in it. Maybe it was all those things, but no matter what the reason, you were in love with the guy. It was something uncontrollable that just creeped up on you and never let go. 

When you hit your teen years was when you really felt it. Every time he brought a new girl to the motel room after school or you caught him making out with some pretty girl in some new "hidden" location, your heart would feel a twinge of pain a little worse than the last. But you kept your mouth shut, trying to push it away into the depths of your heart and mind. You knew he would never feel that way about you, and sure, it hurt like hell, but you tried not to let it get the best of you. So you tried to make it go away. You would help him find new girls to pursue. It never worked. If anything, it made your feelings for him stronger. 

And now, here you are, in your late twenties, coming back from another hunt with the Winchester brothers, thinking about your one-sided love again. Sam turns in his seat to face you, and you snap from your daydreaming. 

"Y/N, did you hear me?" He looks at you, eyebrows raised. 

"Hm? Oh, sorry. I was just... thinking about the hunt." You shake your head to get the thought out of your mind, and sit up straight. "What were you saying?"

"We're getting hungry, and Dean wants to go to Biggerson's, but I want to go to Pita Pit. We need a finalizing vote. Where do you want to go?" He looks at you with his big brown puppy eyes, which basically chant 'Pi-ta Pit! Pi-ta Pit!' You look at him amusingly, but all the while, your mind is on Dean. 

"Sorry, Sam. Can't pass up a Biggerson's sandwich." Dean lifts a fist in the air victoriously. 

"Suck it, Sammy. You can eat a Turducken sandwich like the cool kids." He laughs at Sam, who skulks in the front seat. 

"It's okay, Sam. Biggerson's has salads, too. I think." You try to make him feel better, and he perks up a bit at this. 

"What time is it, Dean?" You ask, noticing how gross you actually are right now. You are covered in a bit of blood, sweat and grime from the hunt, and are desperately in need of a shower before eating. 

"It's 1:26," he answers, checking his watch. 

"Okay, we need to shower before anything else. There's about 20 minutes before we get back to the motel and there's a Biggerson's around the corner from our motel. I don't know about you guys, but I'd rather walk into a restaurant and not take away everyone else's appetite." 

"Agreed." Dean makes a left turn, then speeds up a little. 

The rest of the drive is spent in silence, with the exception of you, thinking about how desperately pathetic you are to have chosen the restaurant the guy you are secretly in love with wanted to go to. 

***

"Dibs on the shower first!" Dean races into the bathroom like a little child, locking it behind him before anyone else can get in there. You shake your head, tossing your bag onto your bed. You shed your jacket and boots, taking out your ponytail and shaking out your H/L H/C hair. 

Soon enough, Dean is out of the shower, freshly shaven and changed. You have to keep your eyes from fluttering shut at the smell of his body wash as he walks by, then stand up to go to have your shower. "Y/N?" Dean calls before you close the door. You stop. 

"Yeah?"

"I'm going to go get the food right now. What do you want?"

"Just a burger and fries," you call over your shoulder as you close the door. 

The shower is heavenly; the warm water hits your shoulders, washing away the grit and soothing your tense muscles. You sigh in pleasure as you lather your hair in its sweet smelling passion fruit shampoo and rinse it out again. You wash your body with your cocoa butter body wash and then step out of the shower. 

You change and walk out of the bathroom, and Sam walks passed you into the bathroom next. 

About ten minutes later, Dean walks into the room loudly. "I come bearing food," he calls heroically. 

You walk up and take the bag from him hungrily. "Woah, woah, little lady. Slow down a bit," he teases. You stick out your tongue and set the bag down, pulling out a burger and fries. 

The three of you eat quickly, hungry from the hunt. No one was badly injured, just a few bumps and bruises from the salt and burn case. Dean finishes first, then he stands up and grabs his jacket. 

"Where are you going?" You ask. 

"There was this chick at the counter at Biggerson's. She finishes her shift in 5 minutes and then we're going to go to a bar. See you guys later," he calls hurriedly over his shoulder. He closes the door behind him and you slouch in your seat. 

Damn it. Even when you're not trying, you manage to get Dean girls that aren't you. You sigh quietly and begin to put away the garbage from your meal. Sam looks at you sadly. "Y/N, can I talk to you?"

"Yeah, Sam?" You look at him, putting on a cheerful face. "What's up?"

"Stop the act. I can see right through it. Y/N, I know how you feel about Dean. I can see it on your face. Why don't you just tell him already?" He looks at you carefully. 

"Hello, have you not seen me? And have you not seen him? Why would he ever want this?" You gesture to your body. 

"What are you talking about, Y/N? You're beautiful." You close your eyes. 

"Uggh, stop trying to make me feel better, Sam. I know the truth. I've seen the girls Dean goes after, and I'm not one of them. I've got no chance. I've tried to forget about it, but I can't. And every time Dean brings some new girl over or goes home with one, it reminds me why I'll never be that girl." You look down, mumbling the last bit. 

Sam lifts your chin and looks at you with care. "Hey, don't think about yourself that way. If Dean can't see what you feel, then maybe he doesn't deserve you." 

"That doesn't make me feel that much better, Sam. Look at me, I'm pathetic. I'm fawning over this guy like a third grader, and it's pathetic. I'm so embarrassed," you laugh weakly. "I feel like such a loser; I'm like those girls I made fun of in high school. God, I'm an idiot. And now, I'm talking to my best friend about it, who happens to be his brother, and I know exactly what you're thinking right now: 'Holy shit, this girl is pathetic.' Just forget it." You start to stand up, but Sam puts a hand on your shoulder.

"Hey, listen to me. You. Are. Not. Pathetic. You're the strongest person I know, who's after a guy who she thinks is out of her league. It's not pathetic, it's a part of life for this to happen at least once in your life." Sam smiles at you reassuringly. "Honestly, though, I think he feels the same way." Your heart stops. 

"What?" You mutter. 

"I think he might be into you, too, Y/N."

"But you just said he didn't deserve me! What do you mean by that?" 

"I was telling you what he probably thinks. Why do you think he's always going after the easiest, least special girls? Because he doesn't think he deserves the most amazing one, so he goes after the ones he knows he can get easily. It's different with you. He- he knows you're not like anyone else. And as your best friend, I don't think anyone deserves you, so there may be that included, too." He smiles sheepishly. You are still in shock. That couldn't be true. Why would Dean want you? He could have anyone, and he nearly has, so what was so special about you?

"What's so special about me?" You voice your thoughts. 

"You're kidding, right? You're an amazing hunter, probably better than Dean in some ways. You're compassionate and kind, but you can be the baddest ass anyone's ever met if you need to be. You're funny, and you basically have the exact same sense of humour as Dean. You prefer beer to water, and eat burgers and fries like it's a religion. You're all over the Impala, and you're faster than Dean to fix a blown tire or busted engine. You're exactly like Dean, if more impressive. You haven't seen the looks he gives you when you're not looking, or known the things he thinks about when you're not around. I know Dean like the back of my hand, and all Dean knows is you." You sit back in shock and wonder. 

"Then why is he out with some girl right now? He practically threw the fact that he was going with her in my face. If he was into me, he wouldn't be that insensitive."

"He's trying to make you think he's not into you, because he's scared you'll reject him. He feels the same way about you that you do about him, even your feelings about whether or not they're reciprocated. He's going after these girls to try to cover the fact that he really only wants you, but he thinks he can't have you. You need to tell him you feel the same, or this shit will never end." Sam answers. He chuckled. "You know, I could be making good money as, like, a psychiatrist for a career, but instead I'm using my skills for my friend and her crush on my brother, when all she should do is call him." He looks at you seriously. "Now."

"Okayy," you hold your hands up in surrender before pulling out your phone and dialing his number. 

"Really listen to his voice when he hears yours," Sam tells you. Dean answers on the second ring. 

"Hello?"

"Hey, Dean, it's Y/N."

"Hey, Y/N, what's up?" Your eyes widen. Is it just you, or did Dean's voice sound more excited right then? You shake your head, chalking it up to nothing. It couldn't be. 

"Um, shouldn't you be on a date right now?" You ask. 

"Oh, uh, she had to go home; an emergency with her roommate or something, she said. So I went to the bar down the street." Dean answers quickly. 

Sam is listening in, and mouths for you to go meet him. "Mind if I come meet you? I could really go for a beer right now," you ask. 

"O-oh, yeah, sure. Why not?" You can hear Dean trying to play it cool, and you fight back a smile. 

"Great, see you soon," you say. 

"Yeah, see you." You hang up, grabbing your jacket. 

"Later, Sam," you chime as you leave the room. 

The bar is within walking distance, so you shrug on your jacket and walk against the soft wind. 

Soon, the glowing blue and red sign reading Jim's Brewhouse comes into view. You step inside and spot Dean slouching at the bar. You walk up to him, sitting on the stool beside him. "Yeah, I'll have a scotch on the rocks," you ask the bartender. He nods and reaches for a bottle of Jack Daniel's whiskey from the shelf. 

Dean looks up at you as you speak, swirling his whiskey in his glass. "Sam hanging back at the motel?" Dean asks, and you can sense tension in his voice. 

"Yeah, he wanted to do some stuff on his laptop." You answer as you take a sip from your whiskey. "I, uh, I also wanted to, um, talk to you about… something." You turn to him. He looks at you expectantly, but as you open your mouth, you realize this is going to be harder than you thought. I'm going to need at least one more whiskey before I can do this, you think. "Never mind, it can wait." You say hurriedly before going back to your drink. Dean looks at you curiously, but turns back to his drink as well. 

You finish your drink in silence, then order another one. It's a quiet night at the bar, and it's rather tame in the alcohol-ridden atmosphere. Somewhere between your second glass of whiskey and first bottle of beer, Let It Be by The Beatles starts to gently flow throughout the room. You close your eyes and listen to the beautiful song, and Dean smiles at the sight of you. He knows this is one of your favorite songs, and realizes that this could be the long shot he was waiting for. 

He stands up and takes your hand, pulling you up gently from your seat. You look at him questioningly, and he smiles at you. "May I have this dance?" He says, obviously mocking the cheesy chick flick films where the guy tries to be romantic in asking the girl to dance in such a manner. 

"Of course," you smile softly. He doesn't say anything else; he just pulls you to the dance floor, where a few other couples have begun to slow dance. He takes one of your hands in his and puts his other on your waist gently. He pulls the hand that is intertwined with yours to his chest, and you rest your free hand on the back of his neck. You both sway to the music, and eventually, you rest your head on his shoulder, not caring if it makes things awkward. You could thank the whiskey for your liquid courage. You open your mouth, letting the whiskey do the job you had intended for it in the first place. "Dean?" You ask quietly. 

"Yes, Y/N?" He answers softly. 

"I want to tell you what I was going to say at the bar."

"Okay, let it out."

You take a deep breath. "I don't know if you feel the same or if Sam was just trying to make me feel better, but, I think I may have feelings for you. Okay, I definitely do, and it's gotten really hard to keep it a secret lately. I honestly get it if you don't feel the same, well, actually, I'm kind of expecting it, but I need you to tell me the truth. This is probably kind of an awkward thing to say while I'm slow dancing with you, but I couldn't really keep it in any longer." Dean stops dancing, and looks at you. 

"What did Sam tell you?" 

You take your head from his shoulder and look up at him. "He said that you have feelings for me. I don't know, he was probably just making it up. This is really embarrassing, I'm sorry, just forget I said anything. I'll just go." You attempt to walk away, but he just holds you tighter. 

"Why would you think he would make it up?"

"Because, I'm… me, and you're always out with these crazy hot girls, and I'm nothing like them." You shrug. 

"What are you talking about? That's the best part about you. You're nothing like those other girls, and you're better than all of them. You're better than them. Too good to be like them. Too good… for me." He looks at you, defeated, and it breaks your heart. "You'd never want someone like me, so I went after girls I knew I could get, which I thought only drove you further from me. Why would you want me?" 

"Are you kidding me, Dean? I've loved you since high school, but you were - and still are - way out of my league! I was too embarrassed, and I really did not want to damage our friendship." 

"Out of your league? You're way out of my league!"

"I guess we were out of each other's league," you say quietly, smiling timidly. 

"Yeah, I guess so," Dean says, slowly leaning closer to you. He stops a fraction of an inch from your lips. "Can I, um," he says shyly. Your lips turn up at the corners, and you nod, closing the gap between your lips. His lips are soft and plump, and you can taste the traces of whiskey left on them. The kiss is short and gentle, yet passionate at the same time, and it says everything the two of you had meant to say. Feel Like Makin' Love by Bad Company sounds through the room from the jukebox in the corner of the room. 

You pull away half a centimeter. "Out of each other's league," you whisper, smiling against his lips. He smiles, too, and he pulls you back to him, swaying to the music once again. 

~ The End ~

**Author's Note:**

> Thank you for reading, let me know what you think. Once again, please only constructive and/or positive comments.
> 
> Keep smiling, my lovelies :)
> 
> -CuriousBones


End file.
